Car Boot Sale

April 6th marks the 3rd annual Boot Sale at the Woodstock Historical Society. It'll run from 8:30 to 2pm and will be catered as in the past. This year we will attempt to have a raffle as well as the sale of our book A journey through Woodstock.

I would love to see you return. Come and have a free cup of coffee on me. The areas are bigger this year but the fee has stayed the same.

This is one of our few fund raisers and we would really appreciate your support.

Call or text Tony at 860-771-1571 to reserve space or just ask questions.

The Original Woodstock

The Town of Woodstock was originally settled in 1686 as New Roxbury by thirteen men (the Goers) from Roxbury, Massachusetts and became the first town in present day Windham County. Thirty families followed the Connecticut path west from Boston and settled in Wabbaquasset. The first homesteads were set up on Plaine Hill and the Westward Hill. Located on the conjunction of three Indian trails, the area was frequented by traders and was situated on the "great road from Hartford to Boston, and on the road from Providence to Albany." Woodstock has thrived since the early days and has played its part in history.  The Commons served as assembly sites for troops during the American Revolution, The War of 1812, and the Civil War. Roseland Cottage hosted Presidential visits in the nineteenth century. Please visit the Woodstock Historical Society Welcome Center next time you are in town and learn more about the fascinating history of our early New England town.